2. Addition reactions
1. For each of the following reactions predict the major organic product. Pay particular attention to the
regiochemistry and stereochemistry.
d) e)
CH3
O
CH3 CH3
a)
c) CH2
b)
H2, Pd/C
HBr
HBr
HBr
HBr
Cl
H3C
2 HBr
CH3 H3C i)
f) H3C
CH2
g) h) CH2
j)
!
HC CH3
HBr Br2
HBr
HBr
H3C H3C
H3C
k)
CH3
CH2 H3C
l) HBr, peroxides n)
m)
CH2
CH3
H+, H2O
HBr, peroxides
CH3
H+, H2O
CH3
1. BH3 / THF
q)
o)
p) H2 / Pt
1. BH3 / THF
H3C 2. H2O2, OH-
1. B2H6 / THF
CH3 H3C
r)
CH3
CH3
CH3 2. H2O2, OH-
2. H2O, H+
CH3
H3C CH3
s)
u)
H3C NBS, h , CCl4
½
CH2
H3C
CH3
Br2 t) CH3
v)
NBS, H2O, DMSO
HOBr
CH2
H3C
H3C CH3
x)
CH3
y)
CH3
w)
CHCl3, KOH
1. RCOOOH
H3C
1. Hg(AcO)2 / H2O
CH3
2. H2O, H+
CH3
2. NaBH4
z)
A)
CH3
CH3 B)
CH3
1. O3
KMnO4, H2O, OH-
KMnO4, H2O, H+
2. Zn, H+
HO
OH
CH3
2. From which alkene could the following compounds be made
a)
b)
(suggest a synthesis):
CH3 H3C
OH
CH3
HO
c)
d)
e)
H3C CH3 H3C
CH3
H3C CH3 CH3 H3C
f)
OH
O
CH3 OH
CH3
CH3 OH
CH3 O
CH3
OH
g) i)
h) j)
CH3
k)
CH3 H OH
Br
H OH
H3C
m) Cl
CH3
n) CH3
l)
O
O
CH3
Cl
CH3
H3C
3. Draw the three-dimensional structures for the
products of the following reactions of
(1R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene:
CH3
4. Suggest a synthesis of: a) butanone and butyraldehyde from 1-butyne; b) 2-methyl-1-butanol from butanone.
C
/
d
P
,
2
H
r
B
2
B
H
/
2
T
H
6
F